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Issue 14, 2018
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Synthesis and structural elucidation of a dehydrochloromethyltestosterone metabolite

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Abstract

The human urinary long-term metabolite “M3” (4-chloro-17β-hydroxymethyl-17α-methyl-18-norandrost-13-en-3-ol) of the common doping agent DHCMT has thus far been detected via GC/MS-MS, creating ambiguities concerning its absolute configuration. Its structure was elucidated via the synthesis of all eight possible stereoisomers with 17β-hydroxymethyl configuration. The highlights of the synthesis consist of a novel first generation approach to 4β-chloro-5β compounds as well as a divergent route which allows easy access to the remaining A-ring chlorohydrins.

Graphical abstract: Synthesis and structural elucidation of a dehydrochloromethyltestosterone metabolite

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Publication details

The article was received on 15 Jan 2018, accepted on 06 Mar 2018 and first published on 06 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00122G
Citation: Org. Biomol. Chem., 2018,16, 2508-2521
  • Open access: Creative Commons BY-NC license
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    Synthesis and structural elucidation of a dehydrochloromethyltestosterone metabolite

    N. Kratena, S. M. Pilz, M. Weil, G. Gmeiner, V. S. Enev and P. Gärtner, Org. Biomol. Chem., 2018, 16, 2508
    DOI: 10.1039/C8OB00122G

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